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US6395765B1 - Antiparasitic composition for the treatment and protection of pets - Google Patents

Antiparasitic composition for the treatment and protection of pets Download PDF

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Publication number
US6395765B1
US6395765B1 US08/719,942 US71994296A US6395765B1 US 6395765 B1 US6395765 B1 US 6395765B1 US 71994296 A US71994296 A US 71994296A US 6395765 B1 US6395765 B1 US 6395765B1
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Prior art keywords
composition
haloalkyl
alkyl
radical
composition according
Prior art date
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Expired - Lifetime
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US08/719,942
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English (en)
Inventor
Jean Pierre Etchegaray
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Boehringer Ingelheim Animal Health France SAS
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Merial SAS
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Priority claimed from FR9511685A external-priority patent/FR2739254B1/fr
Application filed by Merial SAS filed Critical Merial SAS
Assigned to RHONE MERIEUX reassignment RHONE MERIEUX ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ETCHEGARAY, JEAN PIERRE
Assigned to MERIAL reassignment MERIAL CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: MERIEUX, RHONE
Priority to US10/118,404 priority Critical patent/US6867229B2/en
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Publication of US6395765B1 publication Critical patent/US6395765B1/en
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides

Definitions

  • the present invention relates to a composition for the treatment and protection of animals which are infested with parasites or likely to be infested with them.
  • the aim of the invention is to control and eliminate the parasites which infest pets, and especially cats and dogs.
  • ticks (Rhipicephalus sp., Ixodes sp., Dermacentor sp., Amblyoma sp. and the like)
  • Fleas cause an animal a great deal of stress and are harmful to its health. Moreover, fleas are also vectors of pathogenic agents, such as dog tapeworm (Dipylidium caninum), and can also attack man.
  • pathogenic agents such as dog tapeworm (Dipylidium caninum)
  • ticks can also cause an animal stress and be harmful to its health. They can also be harmful to man. However, the most serious problem of ticks is that they are the vector of pathogenic agents which may affect the animal as much as man.
  • borrelioses Lyme disease caused by Borrelia burgdorferi
  • babesioses or piroplasmoses caused by Babesia sp.
  • rickettsioses also known as Rocky Mountain spotted fever.
  • Ticks can also release toxins with paralysing and inflammatory properties, these toxins occasionally being fatal.
  • galls are particularly difficult to combat since there are very few active substances which act on these parasites, and they require frequent treatment.
  • the object of the invention is to provide novel antiparasitic compositions for the treatment and protection of animals, these compositions being of great efficacy while at the same time being easy to use.
  • Another object of the invention is to provide such compositions which are easy to use on any type of domestic animal, irrespective of its size and the nature of its coat.
  • Yet another object of the invention is to provide such compositions which are effective and do not need to be sprinkled over the animal's entire body.
  • Yet another object of the invention is to provide such compositions which, when applied locally, will subsequently diffuse over the animal's entire body and then dry, while at the same time avoiding any phenomenon of crystallization as far as possible.
  • Yet another object of the invention is to provide such compositions which, after drying, do not affect the appearance of the coat and in particular do not leave crystals and do not make the coat sticky.
  • compositions which are useful in particular in the treatment and protection of domestic animals which are infested with parasites or are likely to be infested with them, these compositions comprising, in the form of a ready-to-use solution:
  • R 1 is a halogen atom, CN or methyl
  • R 2 is S(O) n R 3 or 4,5-dicyanoimidazol-2-yl or haloalkyl;
  • R 3 is alkyl or haloalkyl, for example lower haloalkyl
  • R 4 represents a hydrogen or halogen atom; or a radical NR 5 R 6 , S(O) m R 7 , C(O)R 7 or C(O)OR 7 , alkyl, haloalkyl or OR 8 or a radical —N ⁇ C (R 9 ) (R 10 );
  • R 5 and R 6 independently represents a hydrogen atom or an alkyl, haloakyl, C(O)alkyl, S(O) r CF 3 , acyl or alkoxycabonyl radical; or R 5 and R 6 may together form a divalent alkylene radical which may be interrupted by one or two divalent hereto atoms such as oxygen or sulphur;
  • R 7 represents an alkyl or haloalkyl radical
  • R 8 represents an alkyl or haloalkyl radical or a hydrogen atom
  • R 9 represents an alkyl radical or a hydrogen atom
  • R 10 represents a phenyl or heteroaryl group optionally substituted with one or more halogen atoms or groups such as OH, —O-alkyl, —S-alkyl, cyano or alkyl;
  • Y represents a halogen atom or a haloalkyl or haloalkoxy radical, for example a lower haloalkoxy radical, or an SF 5 radical, with the possibility that:
  • Y is CN or NO 2 in positions 2 and 6 (with reference to the carbon of the phenyl ring which is attached to the pyrazole ring and designated 1);
  • Y is S(O) q CF 3 in position 4 on the phenyl ring, but preferably haloalkyl, haloalkoxy or SF 5 ;
  • n, q and r represent, independently of each other, an integer equal to 0, 1 or 2;
  • p is an integer equal to 1, 2, 3, 4 or 5, preferably equal to 1, 2 or 3, in particular 3;
  • R 1 when R 1 is methyl, then either R 3 is haloalkyl, R 4 is NH 2 , p is 2, Y in position 6 is Cl, Y in position 4 is CF 3 and the carbon in position 2 of the phenyl is replaced by N; or R 2 is 4,5-dicyanoimidazol-2-yl, R 4 is Cl, p is 3, Y in position 6 is Cl, Y in position 4 is CF 3 and the carbon in position 2 of the phenyl is replaced by ⁇ C—Cl,
  • a crystallization inhibitor which is present, in particular, in a proportion of from 1 to 20% (W/V), preferably from 5 to 15%, this inhibitor satisfying the test according to which: 0.3 ml of a solution A comprising 10% (W/V) of the compound of formula (I) in the solvent defined in c) below, and 10% of this inhibitor, are placed on a glass slide at 20° C. for 24 hours, after which few or no crystals, in particularly fewer than 10 crystals, preferably 0 crystals, are seen with the naked eye on the glass slide,
  • an organic co-solvent having a boiling point below 100° C., preferably below 80° C., and having a dielectric constant of between 10 and 40, preferably of between 20 and 30; this co-solvent may advantageously be present in the composition in a d) /c) weight/weight (W/W) ratio of between 1/15 and 1/2.
  • the solvent is volatile so as to act in particular as a drying promoter, and is miscible with water and/or with the solvent c).
  • insecticidal active substance corresponds to formula (II),
  • R 1 is a halogen atom, CN or methyl
  • R 2 is S(O),R 3 or 4,5-dicyanoimidazol-2-yl or haloalkyl
  • R 3 is alkyl or haloalkyl
  • R 4 represents a hydrogen or halogen atom; or a radical NR 5 R 6 , S(O) m R 7 , C(O)R 7 or C(O)OR 7 , alkyl, haloalkyl or OR 8 or a radical —N ⁇ C(R 9 ) (R 10 );
  • R 5 and R 6 independently represent a hydrogen atom or an alkyl, haloalkyl, C(O)alkyl, S(O) r CF 3 or alkoxy carbonyl radical; or R 5 and R 6 may together form a divalent alkylene radical which may be interrupted by one or two divalent hetero atoms such as oxygen or sulphur;
  • R 7 represents an alkyl or haloalkyl radical
  • R 8 represents an alkyl or haloalkyl radical or a hydrogen atom
  • R 9 represents an alkyl radical or a hydrogen atom
  • R 10 represents a phenyl or heteroaryl group optionally substituted with one or more halogen atoms or groups such as OH, —O-alkyl, —S-alkyl, cyano or alkyl;
  • R 11 and R 12 represent, independently of each other, a hydrogen or halogen atom and possibly CN or NO 2 , but with H or halogen being preferred;
  • R 13 represents a halogen atom or a haloalkyl, haloalkoxy, S(O) q CF 3 or SF 5 group;
  • n, q and r represent, independently of each other, an integer equal to 0, 1 or 2;
  • X represents a trivalent nitrogen atom or a radical C—R 12 , the other three valencies of the carbon atom forming part of the aromatic ring;
  • R 1 when R 1 is methyl, then either R 3 is haloalkyl, R 4 is NH 2 , R 11 is Cl, R 13 is CF 3 and X is N; or R 2 is 4,5-dicyanoimidazol-2-yl, R 4 is Cl, R 11 is Cl, R 13 is CF 3 and X is ⁇ C—Cl.
  • the alkyl radicals in the definition of the compounds of formulae (I) and (II) generally comprise from 1 to 6 carbon atoms.
  • the ring formed by the divalent alkylene radical representing R 5 and R 6 , along with the nitrogen atom to which Rs and R 6 are attached, is generally a 5-, 6- or 7-membered ring.
  • R 1 is CN
  • R 3 is haloalkyl
  • R 4 is NH 2
  • R 11 and R 12 are, independently of each other, a halogen atom
  • R 13 is a haloalkyl.
  • X is C—R 12 .
  • a compound (A) of formula (I) which is most particularly preferred in the invention is 1-[2,6-Cl 2 4-CF 3 phenyl] 3-CN 4-[SO-CF 3 ] 5-NH 2 pyrazole, whose common name is fipronil.
  • the compounds of formula (I) may be prepared according to one or other of the processes described in patent applications WO-A-87/3781, 93/6089 and 94/21606 or European patent application EP-A-295,117, or any other process which falls within the competence of a specialist skilled in the art of chemical synthesis.
  • a person skilled in the art is considered as having at his disposal, inter alia, all of the contents of “Chemical Abstracts” and of the documents which are cited therein.
  • composition may optionally comprise water, in particular in a proportion of from 0 to 30% (volume per unit volume V/V), in particular from 0 to 5%.
  • composition may also comprise an antioxidant intended to inhibit aerial oxidation, this agent being present in particular in a proportion of from 0.005 to 1% (W/V), preferably from 0.01 to 0.05%.
  • compositions according to the invention intended for pets, in particular cats and dogs are generally applied by deposition on the skin (“spot on” or “pour on” application); this is generally a localized application to a region with a surface area of less than 10 cm 2 , especially between 5 and 10 cm 2 , in particular at two points and preferably localized between the animal's shoulders.
  • spot on or “pour on” application
  • the composition diffuses, in particular over the animal's entire body, and then dries, without crystallizing or changing the appearance (in particular absence of any whitish deposit or of any dusty appearance) or the feel of the coat.
  • compositions according to the invention are particularly advantageous on the grounds of their efficacy, their speed of action and the pleasant appearance of the animal's hair after application and drying.
  • organic solvent c) which can be used in the invention, mention may be made in particular of: acetone, acetonitrile, benzyl alcohol, butyl diglycol, dimethylacetamide, dimethylformamide, dipropylene glycol n-butyl ether, ethanol, isopropanol, methanol, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, monomethylacetamide, dipropylene glycol monomethyl ether, liquid polyoxyethylene glycols, propylene glycol, 2-pyrrolidone, in particular N-methylpyrrolidone, diethylene glycol monoethyl ether, ethylene glycol, diethyl phthalate, or a mixture of at least two of these solvents.
  • the preferred solvents c) are the glycol ethers, in particular diethylene glycol monoethyl ether and dipropylene glycol monomethyl ether.
  • crystallization inhibitor b which can be used in the invention, mention may be made in particular of:
  • polyvinylpyrrolidone polyvinyl alcohols, copolymers of vinyl acetate and vinylpyrrolidone, polyethylene glycols, benzyl alcohol, mannitol, glycerol, sorbitol, polyoxyethylenated sorbitan esters; lecithin, sodium carboxymethylcellulose; acrylic derivatives such as methacrylates and the like,
  • anionic surfactants such as alkaline stearates, in particular sodium, potassium or ammonium stearate; calcium stearate, triethanolamine stearate; sodium abietate; alkyl sulphates, in particular sodium lauryl sulphate and sodium cetyl sulphate; sodium dodecylbenzenesulphonate, sodium dioctylsulphosuccinate; fatty acids, in particular those derived from coconut oil,
  • cationic surfactants such as water-soluble quaternary ammonium salts of formula N + R′R′′R′′′R′′′′ Y ⁇ in which the radicals R are hydrocarbon radicals, optionally hydroxylated, and Y is an anion of a strong acid such as halide, sulphate and sulphonate anions; cetyltrimethylammonium bromide is among the cationic surfactants which can be used,
  • nonionic surfactants such as optionally polyoxyethylenated sorbitan esters, in particular polysorbate 80, polyoxyethylenated alkyl ethers; polyethylene glycol stearate, polyoxyethylenated derivatives of castor oil, polyglycerol esters, polyoxyethylenated fatty alcohols, polyoxyethylenated fatty acids, copolymers of ethylene oxide and propylene oxide,
  • amphoteric surfactants such as lauryl-substituted betaine compounds, or preferably a mixture of at least two of these crystallization inhibitors.
  • crystallization inhibitor system namely the combination of a film-forming agent of polymer type and a surfactant.
  • These agents will be chosen in particular from the compounds mentioned as crystallization inhibitor b).
  • film-forming agents of polymer type which are particularly advantageous, mention may be made of:
  • nonionic surfactants preferably polyoxyethylenated sorbitan esters and in particular the various grades of polysorbate, for example polysorbate 80.
  • the film-forming agent and the surfactant may in particular be incorporated in similar or identical amounts within the limit of the total amounts of crystallization inhibitor which are mentioned elsewhere.
  • the system thus made up achieves, in a noteworthy manner, the aims of absence of crystallization on the hair and of maintenance of the cosmetic appearance of the coat, that is to say without a tendency to stick together or to have a sticky appearance, despite high concentration of active substance.
  • co-solvent d mention may be made in particular of: absolute ethanol, isopropanol (2-propanol), methanol.
  • antioxidant standard agents are used in particular, such as: butylated hydroxyanisole, butylated hydroxytoluene, ascorbic acid, sodium metabisulphite, propyl gallate, sodium thiosulphate, a mixture of not more than two of these antioxidants.
  • compositions according to the invention are usually prepared by simply mixing the constituents as defined above; advantageously, to begin with, the active substance is mixed into the main solvent, and the other ingredients or adjuvants are subsequently added.
  • the subject of the present invention is also a method for the treatment and/or protection (preventive care) of animals against parasites, according to which an effective volume of a composition according to the invention is applied to a limited area of the animal, as is described above.
  • the application is advantageously made at two points and/or on the animal's back between the shoulders.
  • the aim of the method may be non-therapeutic, when it concerns cleaning the animal's hair and skin by eliminating the parasites present as well as their residues and excreta.
  • the animal thus has a coat which is pleasant to look at and to feel. This also makes it possible to prevent the establishment of fleas in the house.
  • the aim may also be therapeutic when it concerns treating a parasitosis which has pathogenic consequences.
  • the volume applied may be about 0.3 to 1 ml, preferably about 0.5 ml for cats, and about 0.3 to 3 ml for dogs, depending on the weight of the animal.
  • the volume of composition applied preferably corresponds to a dose of compound of formula (I) of between 0.3 and 60 mg, in particular of between 5 and 15 mg, per kg.
  • compositions of Examples 1 to 12 are given in the following table:
  • the volume of diethylene glycol monoethyl ether represented by qs is about 75 cm 3 for the formula of Example 1.
  • the mixture is made up to 100 cm 3 with diethylene glycol monoethyl ether or with dipropylene glycol monomethyl ether (for Example 1, this corresponds to a remaining volume of about 15 cm 3 ).
  • Examples 12 to 24 it suffices to replace, in the above table, Examples 1 to 12 by 12 to 24 respectively, with 12.5 g of active principle.
  • the amounts of the other constituents are unchanged, apart from the amount of solvent required for the complement to 100 cm 3 .
  • the mixture is made up to 100 cm 3 with diethylene glycol monoethyl ether or with dipropylene glycol monomethyl ether.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Environmental Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Dermatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicinal Preparation (AREA)
  • Feed For Specific Animals (AREA)
  • Fodder In General (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
US08/719,942 1995-09-29 1996-09-25 Antiparasitic composition for the treatment and protection of pets Expired - Lifetime US6395765B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US10/118,404 US6867229B2 (en) 1995-09-29 2002-04-08 Antiparasitic composition for the treatment and protection of pets

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR9511685A FR2739254B1 (fr) 1995-09-29 1995-09-29 Composition antiparasitaire pour le traitement et la protection des animaux de compagnie
FR9511685 1995-09-29
FR9611278A FR2739255B1 (fr) 1995-09-29 1996-09-11 Composition antiparasitaire pour le traitement et la protection des animaux de compagnie
FR9611278 1996-09-11

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US10/118,404 Division US6867229B2 (en) 1995-09-29 2002-04-08 Antiparasitic composition for the treatment and protection of pets

Publications (1)

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US6395765B1 true US6395765B1 (en) 2002-05-28

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US08/719,942 Expired - Lifetime US6395765B1 (en) 1995-09-29 1996-09-25 Antiparasitic composition for the treatment and protection of pets
US10/118,404 Expired - Lifetime US6867229B2 (en) 1995-09-29 2002-04-08 Antiparasitic composition for the treatment and protection of pets

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Application Number Title Priority Date Filing Date
US10/118,404 Expired - Lifetime US6867229B2 (en) 1995-09-29 2002-04-08 Antiparasitic composition for the treatment and protection of pets

Country Status (30)

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US (2) US6395765B1 (fr)
EP (1) EP0881881B1 (fr)
JP (4) JP3765891B2 (fr)
KR (1) KR100348204B1 (fr)
CN (1) CN1122443C (fr)
AR (1) AR004002A1 (fr)
AT (1) ATE236529T1 (fr)
AU (1) AU720952C (fr)
BE (1) BE1009819A3 (fr)
BR (1) BR9603919A (fr)
CA (1) CA2204745C (fr)
CO (1) CO4770950A1 (fr)
DE (1) DE69627384C5 (fr)
DK (1) DK0881881T3 (fr)
ES (1) ES2191766T3 (fr)
FR (1) FR2739255B1 (fr)
GR (1) GR1002767B (fr)
IL (1) IL120750A (fr)
IT (1) IT1285002B1 (fr)
MX (1) MX9703966A (fr)
MY (1) MY118356A (fr)
NL (1) NL1004155C2 (fr)
NO (1) NO320526B1 (fr)
NZ (1) NZ319193A (fr)
PE (1) PE18998A1 (fr)
PT (1) PT881881E (fr)
RU (1) RU2160535C2 (fr)
TW (1) TW442261B (fr)
UY (1) UY24334A1 (fr)
WO (1) WO1997012521A1 (fr)

Cited By (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020151577A1 (en) * 1995-09-29 2002-10-17 Etchegaray Jean Pierre Antiparasitic composition for the treatment and protection of pets
US20030134877A1 (en) * 2000-06-16 2003-07-17 Centers For Disease Control And Prevention, An Agency Of Us Department Of Health & Human Services Control of arthropods in rodents
US20030161854A1 (en) * 2000-03-20 2003-08-28 Lowe Lionel Barry Synergistic formulations
US20040077703A1 (en) * 2002-10-02 2004-04-22 Soll Mark D. Nodulisporic acid derivative spot-on formulations for combating parasites
US20040244717A1 (en) * 2000-06-16 2004-12-09 Maupin Gary O. Apparatus for applying chemicals to rodents
US20040253725A1 (en) * 2000-06-16 2004-12-16 Centers For Disease Control And Prevention Control of arthropod vectors of parasitic diseases
US20070164129A1 (en) * 2006-01-04 2007-07-19 Nano Mist International, Llc Air driven delivery system for sprayable media
WO2008080541A1 (fr) * 2006-12-27 2008-07-10 Bayer Animal Health Gmbh Agents de lutte contre les parasites chez l'animal
US20080194642A1 (en) * 2007-02-09 2008-08-14 Wyeth High dose, long-acting ectoparasiticide for extended control
WO2008080542A3 (fr) * 2006-12-27 2008-08-28 Bayer Healthcare Ag Produit de combinaison destiné à la lutte contre les parasites chez l'animal
US20090137524A1 (en) * 2003-12-18 2009-05-28 Denis Billen Substituted arylpyrazoles
US20090192207A1 (en) * 2003-12-17 2009-07-30 Albert Boeckh Topical Formulations Comprising 1-N-Arylpyrazole Derivatives and Amitraz
US20090197896A1 (en) * 2008-02-02 2009-08-06 Meidong Yang Methods and compositions for increasing solubility of azole drug compounds that are poorly soluble in water
WO2010026370A1 (fr) * 2008-09-05 2010-03-11 Norbrook Laboratories Limited Composition ectoparasiticide locale
US20100099668A1 (en) * 2006-09-01 2010-04-22 Frank Guerino Local topical administration formulations containing indoxacarb
EP1601249A4 (fr) * 2003-02-26 2010-05-12 Merial Ltd Derives de 1-n-arylpyrazole utilises dans la prevention de maladies vehiculees par les anthropodes ou par les moustiques
US20100125097A1 (en) * 2008-11-19 2010-05-20 Mark David Soll Compositions comprising an aryl pyrazole and/or a formamidine, methods and uses thereof
WO2010065852A1 (fr) 2008-12-04 2010-06-10 Merial Limited Dérivés dimères d'avermectine et de milbémycine
US20100197620A1 (en) * 2001-09-17 2010-08-05 Eli Lilly And Company Pesticidal formulations
WO2011014660A1 (fr) 2009-07-30 2011-02-03 Merial Limited Composés insecticides à base de 4‑amino-thiéno[2,3-d]pyrimidine et leurs méthodes d'utilisation
US20110060023A1 (en) * 2009-03-18 2011-03-10 Donnelly Martin Benedict George Parasiticidal formulation
WO2011035288A1 (fr) 2009-09-21 2011-03-24 Merial Limited Formulations à versage et à pulvérisation de suspension aqueuse et de solution non aqueuse à base de dicyclanile pour la prévention et le traitement d'infestation par des insectes chez des animaux
WO2011069143A1 (fr) 2009-12-04 2011-06-09 Merial Limited Composés pesticides bis-organosulfurés
WO2010092355A3 (fr) * 2009-02-16 2011-06-23 Cipla Limited Composition topique
WO2011075591A1 (fr) 2009-12-17 2011-06-23 Merial Limited Dihydroazoles antiparasitaires et compositions les incluant
WO2011075592A1 (fr) 2009-12-17 2011-06-23 Merial Limited Compositions contenant des composés de lactone macrocyclique et des spiro-dioxépino-indoles
WO2011092604A2 (fr) 2010-01-29 2011-08-04 Pfizer Inc. Formulations antiparasites topiques
WO2011123773A1 (fr) 2010-04-02 2011-10-06 Merial Limited Compositions parasiticides comportant de multiples principes actifs, procédés et utilisations associés
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EP0881881B1 (fr) 2003-04-09
MY118356A (en) 2004-10-30
FR2739255A1 (fr) 1997-04-04
JP5989626B2 (ja) 2016-09-07
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TW442261B (en) 2001-06-23
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IL120750A0 (en) 1997-09-30
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US6867229B2 (en) 2005-03-15
PT881881E (pt) 2003-07-31
JP5057667B2 (ja) 2012-10-24
AU720952C (en) 2004-02-12
ATE236529T1 (de) 2003-04-15
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DE69627384T2 (de) 2004-02-12
ITTO960795A1 (it) 1998-03-27
BE1009819A3 (fr) 1997-09-02
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IL120750A (en) 2001-04-30
EP0881881A1 (fr) 1998-12-09
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IT1285002B1 (it) 1998-05-28
FR2739255B1 (fr) 1998-09-04
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US20020151577A1 (en) 2002-10-17
CA2204745A1 (fr) 1997-04-10
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